Bones is clearly talking about Tom Riddle, Jr., who seems to have brilliantly played both sides of the field as he rose to power.
I noticed a typo:
"The old wizard nodded, but his eyes still seemed distant, fixed only on the road head."
Road head is a little bit different from road ahead.
Bones is clearly talking about Tom Riddle, Jr., who seems to have brilliantly played both sides of the field as he rose to power.